Love Across Generations
by CalagrianKnight
Summary: This is a series of Pokemon one shot stories, each one consisting of different characters from around the Pokemon world. Watch as true love unfurls. I only write pairings that I deem good pairings. Rated M for future chapters.
It had been over ten years since his last Pokémon contest, and Drew was sitting at his own bedside with his Roserade. As he silently sat in his dimly lit room, he stared down at his ribbon case from all the contests he's ever won.

"Those were the days, huh Roserade?" The twenty year old coordinator mused towards his flowery Pokémon.

"Rade!" the Roserade happily replied.

As the green haired man stared down nostalgically at his ribbon case, he reminisced on the last contest he had ever taken part in, the Grand Festival. It was a close battle between his team of Flygon and Absol versus his rival's team of Combusken and Squirtle. They fought long and hard, but after multiple dazzling move combinations and the knocking out of both Flygon and Squirtle, it was down to his Absol against her Combusken in a solo one versus one match. With minutes on the clock, Drew desperately tried to barrage his opponent with Razor Wind and Iron Tail to take it out, but it wasn't enough to take it out. In the end, his rival, May, ended up winning the battle after the battle timer reached zero. He felt sad to have lost, but proud to have witnessed his rival grow into an excellent co-ordinator equal to or beyond his own skill level. Hours later, Drew watched from afar to see that May's team was decimated by Solidad, a friend and roommate of his of whom he had lost his first ever contest to. After that, Drew decided to leave the contest hall to start his newest journey in the Johto region. Before he could get out of sight, May came bursting through the front door of the contest hall.

"Drew!" She called out, running as fast as she could towards her green haired associate. Drew turned his head and waited for May to catch her breath from running. "See you in a contest or something!" She exclaimed. Silently they stood there until Drew smiled and broke the silence.

"Yeah, no doubt, May," Drew proclaimed, making May noticeably ecstatic. She gave a small laugh of excitement before Drew turned back to his previous path. "Kay, bye," he said as he walked away, leaving his signature rose in the possession of May.

He had his mind set on going for a circuit of contests in the Johto region, but unfortunately, he never got the chance. Having had his fill of contests for a while, Drew decided to take a break and return to his hometown of LaRousse City, where he inadvertently ran into two of the coordinators from the Grand Festival: Harley, a tall violet haired male trainer with an outfit resembling a Cacturne, and Solidad, the pink haired woman who had beaten both him and May on past occasions. When the three co-ordinators all reached adult age, they all got together and moved into the same house as roommates. Drew was happy, but, no matter what good thing came his way, whether it be with his Pokémon or his friends, there was always this feeling that something was missing from his life, something greater than all of his accomplishments combined.

"May," Drew quietly murmured to himself as he stroked his ribbon case with his thumb gently. The man's flowery Pokémon, hearing her trainer's forlorn muttering, looks over, worried for his wellbeing.

"Rose?" The Roserade calmly and caringly whimpered. Drew sullenly looked up at his Roserade and smiled.

"Sorry Roserade," the former co-ordinator apologized, gently petting the dainty white petals on her head. "I was just thinking out loud is all. No need to be concerned." Roserade could tell that her trainer was lying, but decided to not think too much into it.

As Drew sat in his dim room, brooding over his contest memories, he heard a knock on the door. "Who is it?" Drew asked. Not even two seconds after that, his roommate, Solidad, opened the door and entered his room unannounced.

"It's just me, Drew," she slyly replied, leaning against his door frame. "Just coming in to check in on you and see how you're doing."

"Well, as you can see, I'm fine," Drew assured, still holding his ribbon case in his hands. Solidad walks over and sits by Drew.

"Still reminiscing over your days as a coordinator, huh?" Solidad asked. Drew can only nod in response. "Well, it's obvious you miss doing contests, so why not just go back?"

"I don't know," Drew replied somberly. "I guess I just lost interest is all."

"But if you lost interest, then why are you-" Solidad stopped herself when she began to get the bigger picture. "-oh, I think I know what's going on here." She scooted closer to Drew and put a single hand on his shoulder comfortingly. "You miss her, don't you?" This remark made Drew blush ever so slightly.

"Yeah," he sullenly responded. Solidad sighs a bit.

"Listen, Drew, I've had my fair share of boyfriends throughout the years since then, so if you need to talk to anyone about this subject, I'm basically your best bet." Solidad consoled. "May is a very intriguing girl, so I can see why you have feelings for her. She's very skilled in what she does."

"I think I saw her in a contest on TV about a year or two ago. It could have been someone else that looked like her, but to my knowledge, I'm pretty sure it was her." Drew hesitantly retaliated.

"Yeah, that was her," Solidad confirmed. "I've been keeping in contact with her ever since the Grand Festival ten years ago. She called me on my PokeNav the other day and told me about her latest contest, which went over in her favor rather easily ever since I started giving her some tips and tricks a few years back. Apparently she won last year's Grand Festival by learning from my advice. Isn't that awesome?"

"Yup, pretty awesome," Drew dourly agreed, still thinking about May fondly. Solidad, obviously worried about her green haired friend, cracks a smile and looks over to him.

"Hey, don't beat yourself up for not pursuing her actively," Solidad remarked. "Hey, I have an idea. Why don't we plan a trip to Petalburg City some time?" Drew, mildly amazed by his friend's suggestion, turns his head over to her.

"A trip to Petalburg," Drew curiously repeated. "are you serious?

"Of course I'm serious," Solidad cheerfully responded. "It could be a vacation of sorts. All three of us could go, you, me, and Harley even."

"Does Harley have to come?" Drew annoyedly questioned. "Harley isn't exactly the most well behaved person in the world you know."

"Well, I can agree with you there," Solidad wholeheartedly responded. "Tell you what, how about just the two of us go? We can leave Harley here to look over the house while we're away. Does that sound good to you?" Drew smiled, nodding happily.

 _5 days later_ -

"Alright Harley, we're off," Solidad called back from outside. "Don't wreck the house too badly while we're gone."

"Please, leave the jokes aside this time, Solidad," Harley responded, leaning on the frame of the front door and smirking slyly. "Have a nice trip you two, and don't do anything I wouldn't do." Solidad, knowing that Harley is joking, chuckled slightly at her roommate's quip before heading off with Drew to the LaRousse Airport so that they can fly to Petalburg City.

"Remind me why we're not using Pidgeot and Flygon to fly there," Drew wondered.

"Well for one, Pidgeot is currently with my friend, so I couldn't ride him even if I wanted to." Solidad answered. "As for Flygon, I'm sure he wouldn't want to fly you all the way to Petalburg City from LaRousse City, would he?

"You got me there, Sol. You got me there," Drew replied, staring blankly at the natural Hoenn scenery around them as they walked across town to the airport.

Once at the airport, the two co-ordinators donned their backpacks and boarded the aircraft that would take them to Petalburg City. Whilst onboard the plane, the two sat quietly, Drew in particular leaning his head into the palm of his hand as he stared out the window at the clouds. Lost in his fantasies, Drew stared longingly at one of the clouds outside the plane window, it's simplistic innocence mirroring that of the woman of his desires, May. The plane ride lasted around five hours, making its descent and final landing late in the afternoon. Once the plane had touched down on the runway and come to a full stop, all passengers were then vacated from the aerial vehicle.

"Well, we're here, Drew," Solidad happily remarked. Drew silently looked around the Petalburg Airport. It was small and had a much more rustic look to it than that of LaRousse City. The two co-ordinators, after exploring the airport for an hour or two, took their things and walked out into the City to see the rest of Petalburg City, the city where people and Pokémon alike freely mingle with the nature around them. Drew and Solidad walk across town, searching for a place they can stay. They end up finding a small inn and getting a two-bed room to share between the two of them. When they enter the room, Solidad quickly put her backpack down on the floor and crashed on the bed furthest from the wall, sprawling out atop the covers.

"Oh man, I'm so glad we're finally here," Solidad says, tired from the journey.

"It hasn't been too long, Sol," Drew clarified. "but I don't blame you for being so tired." Drew sat down at the edge of the remaining bed, staring up at the ceiling. Soon, after setting down his backpack on the bed, Drew got up and headed for the door. "I'm going out for a bit, Solidad. Mind holding the fort until I get back?"

"Sure thing," Solidad faintly replied, still sprawled out across her own bed

Drew smiled back at his pink haired friend as he exited the room, walking out of the inn and around the town aimlessly. He looked over to his right side, the setting sun glowing gently and sinking slowly behind the tree line. As he walked across town, he looked around him, seeing the dimly lit streets as the evening dusk slowly approached. Drew, watching the sun set over the distant horizon, cracked a small smile whilst he walked, but his modest moment of contentedness was about to be cut short. Because he wasn't paying attention to where he was walking, he accidentally bumped into someone else, knocking both him and the other person to the dusty ground below. Drew rubbed his head, trying to take in what had just happened.

"I'm so sorry, I-" Drew's words suddenly got caught in his throat as he witnessed who it was that he bumped into. Out of all the people he could have collided with on his first evening in Petalburg City, it had to be the one he had been longing after for so long, May. "-M-May?" Drew uttered, very nearly choking on his words as a blush quickly spread across his face like a wild brushfire. The woman looked up to see her old green haired friend, just as shocked to see him as he is to see her.

"Drew?" May surprisedly muttered. Soon, her shock rapidly morphed into happiness as she suddenly embraced Drew in a friendly hug, causing Drew's already intense blush to spread even further across his bright red face. "Oh my god, Drew! I haven't seen you in years! How are you? How long has it been? Where have you been this whole time? What have you been doing with yourself? Why are you here?"

"I uh…" Drew was at a loss for words, so Drew remained silent for a few seconds before shaking off his nerves, still somewhat surprised that he ran into May on his first night. "Um, I've been good, I just decided to take a break from contests for a while, and as it turns out, that break was indefinite." Drew rubbed the back of his head out of embarrassment, taking May's hand to help her and him both up onto their feet. "I'm sorry I wasn't able to stay in contact as much as you would have liked me to. I just needed to separate myself from the contests for a while. If it means anything, I did move in with Harley and Solidad a couple years ago."

"You live with Harley?" May questioned. "How's that working out for you?"

"Just about how you would expect it to, I guess. He's obnoxious, self obsessed, and prone to angry outbursts and devious tricks." Drew responded. "but hey, he's not the worst roommate to have around sometimes. I would ask how you've been, but Solidad clued me in on that as we headed here to Petalburg."

"Wait, Solidad's here too?" May asked excitedly. "Awesome! Can we go see her?"

"She's taking a nap right now," Drew mentioned. "The trip here really tired her out somehow."

"Oh, I understand," May replied. Drew, wanting to make the most out of this run in, knew he had to make some sort of move right then and there.

"Hey um, May," Drew began. "I um...I was just wondering if maybe...I don't know...is there a chance that we...uh...we could possibly...you know...do something for a while? Tonight maybe?" Drew's massive blush returned as he finished his statement, an equally large blush appearing on the face of the woman in front of him.

"Uh...sure," May responded, her cheeks a burning shade of red. "What do you want to do?"

"I don't know, are there any places with good views here in Petalburg City?" Drew asked in response.

"Well, there is this one cliff overlook at the south side of the city," May answered. "From there you can see all of Petalburg Woods. Does that seem fitting enough?" Drew smiled, nodding at his friend's statement. The two soon began their trek up the hill that lead to the overlook, both parties staying silent throughout the journey upwards. After a few minutes of scaling the hill, the two coordinators reach the top of the cliff, the view of the woods below breathtaking.

"Whoa," Drew muttered, awestruck by what he was witnessing.

"I know," May responds. "Every time I come up here, it always gives me the same feeling. It's just an amazing sight to see."

"I can tell," Drew responded with. Seconds passed and Drew began to blush a bit again, looking down a bit. "Hey May, mind if I ask you something?"

"Sure, what is it?" May soon responded.

"While you were talking with Solidad all these years, not to seem selfish or anything, did I ever come up into the conversation at all?" Drew inquired, the blush on his face growing more yet again. Soon, May's blush quickly followed suit and spread across her face like mad.

"Heh, it's funny you mention that," May mused. "While, no, you never did come up as a conversation topic, I was constantly thinking about you every time Solidad and I talked." May's blush soon grew even further, covering her entire face in a thick blanket of red hue. "Drew I...I never got you out of my mind after you left. I mean, I neglected to show it at times, yes, but no matter what sort of mood I put on, I was always being reminded of you left and right. Everywhere I looked, I would always find something that made me think of our time together as rivals."

"May, what are you going at?" Drew, curious as to his friend's intent, turned his head towards her, blushing slightly in preparation for what he suspects May was about to tell him.

"Drew, I missed you so much after you left," May continued. "and now that you're back with me here, it's...well...it's basically sending my emotions into a frenzy." She blushed even more, her face resembling a freshly ripened tomato berry. "My heart is telling me to do things that I'm unsure of, but I think that I-" May was suddenly cut off mid sentence as Drew quickly embraced her in a hug, this hug seeming to be more than just a friendly hug as he squeezed her within his arms. As Drew held her tight, May's face was frozen in a shocked state.

"May, you have no idea how long I've had those same feelings for you," Drew blurted out, closing his eyes to enjoy holding May in his embrace. "I've wanted for so long to tell you how I felt about you, and now that you've just told me that my feelings are mutual, you have no idea how much that means to me, May." May blushed worse at Drew's words, shyly and slowly wrapping her arms around him just like his were around her. She rested her her gently on the green haired man's shoulder, still blushing wildly.

"Drew I-" May said in unison with Drew.

"May I-" Drew said in unison with May.

Both paused for a second before continuing to speak. "You first," May quietly uttered. Drew nodded, clearing his throat.

"May I...I love you. I've loved you for a long time, May," Drew exclaimed, looking her deep within her sapphire blue eyes.

"Drew…"May muttered, looking back into Drew's emerald green eyes. "I love you too. At first you were just a friend, but I realized I loved you as soon as you left your rose with me on the night you left." Drew, still astounded that May was returning his feelings for her, closed his eyes yet again, tears of joy lightly trickling down his face from behind his eyelids.

"All this time, I was so worried that you'd forgotten about me," Drew commented.

"I could never, Drew," May reassured, gently placing her hand on Drew's cheek. As the two gazed deeply within each other's eyes, their faces grew ever closer.

"May, do you think we should-" Drew blushed immensely as May suddenly closed any gap between their lips, pulling him into a deep, passionate, love soaked kiss. The green haired man had no objections as he closed his eyes and enjoyed every waking moment of the magical kiss. As the kiss progressed, both parties grew more vigorous, Drew even being so bold as to reach down and gently grasp May's lovely rounded behind. May, while having jumped a bit as Drew groped her, did not seem to mind his actions in the slightest. There the pair remained for the next half hour, the love and passion imbued in the kiss making it seem like mere seconds. After they both had their fill, May and Drew both reluctantly pulled their faces away from each other's. The two panted and peered deeply within each other's eyes yet again, the sun now fully set over the Petalburg horizon.

"Wow," both coordinators proclaimed in unison.

"I love you, May," Drew repeated, holding May in a warm, loving hug still.

"And I love you, Drew," May retorted, enjoying being embraced by her former coordinating rival. The two smiled at each other, remaining in their embrace for a long while before finally breaking off.

"So...I guess that makes us official then?" Drew wondered. May only nodded calmly without a word, both of them still bright red from their blush shrouded faces.

"Now what?" May asked.

"Maybe I could take you over to the inn Solidad and I are staying at," Drew suggested. "After all, it would be a shame if Solidad lost her opportunity to talk with you in person after all this time."

"Seems good to me," May responded, a smile stretching across her bright red face.

"As for tomorrow...do you wanna maybe do something...together, you know, as a couple?" Drew offered. May, held Drew's hand, still smiling brightly at him.

"I'd like that," May answered. Soon, the pair walked back down the hill to the inn, holding hands the entire way down. As they reached the inn, Drew opened the door politely for his new girlfriend. May blushed happily as she placed a quick peck on the cheek of her new boyfriend.


End file.
